


Cherry Red

by mggislife2789 (dontshootmespence)



Category: Supernatural
Genre: 1940s, F/M, Spanking, Vaginal Sex
Language: English
Status: Completed
Published: 2020-01-30
Updated: 2020-01-30
Packaged: 2021-02-26 10:10:01
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,902
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22484731
Author URL: https://archiveofourown.org/users/dontshootmespence/pseuds/mggislife2789
Summary: Ness says they can’t do anything about Chronos until the morning, so what should Dean do all night in 1944?Disclaimer: I don't own any of these characters or their original stories. This is only for fun. It's where my brain goes after the credits roll. No copyright intended. Better safe than sorry. ;)
Relationships: Dean Winchester/Reader, Dean Winchester/You
Comments: 2
Kudos: 13





	Cherry Red

“Kid, we got nothing to kill the bastard and we can’t get it till mornin’, so why not go get some sleep?” Ness asks, deftly flipping his hat onto his head with the flick of his fingers. 

“I’ll sleep when I’m dead.”

He bids Ness goodnight with strict instructions to be back at 5 AM. Even though he feels like he’s in The Untouchables, he needs to get back to Sam as soon as possible. That being said, there’s no way in hell he was going to sleep his way through his free time in 1944. Something tells him there’s some good strong whiskey and a beautiful dame out there somewhere.

As he saunters down the block (he’d say he wasn’t sauntering, but the 1940s garb had him feeling some kind of way), he grabs the brim of his hat and tips it in the direction of anyone and everyone he comes across. He’s so outta place but he plans to play it up for as long as he’s here.

Under his feet, water splashes from freshly fallen rain. The streets around him smell of rain with tinges of cigar smoke, which happens to be coming from a bar named Cahoots.

Opening the door, the bell above it rings, alerting everyone in the bar to the out of place “cop” that just walked in. Deep brown wood is bathed in low light, bottles glistening on the simple shelf before the fellow patrons.

Dean starts to pull up a seat, seeing mostly men around him, but through the fog of cigar smoke he sees her. She scowls at every man who comes near, though most of them are acting like they’d never seen a woman before, coming on too strong thinking they were meat or not coming on strong enough. Sure, Dean had gone to bed with his fair share of women, but he was big on willingness. Their willingness was pretty sexy.

He strides over and gently pushes through the throng of men, ordering a whiskey neat before turning his attention to the woman at his side. “So what’s a beautiful dame like you doing at this bar all alone? Are you rationed?” He asks, feeling every inch Humphrey Bogart.

“How d’ya know I’m alone, g-man?”

Her hair is pinned in waves, perfectly framing her doe eyes - not innocent ones though, they held much more than most would think he’s sure. She’s decked in cherry red, a black belt cinching her waist and matching black heels showing every inch of her beautiful calves. He’s used to seeing more skin on a woman, at least one in a dress, but something about the way she’s dressed intrigues him. He wants to know more. Maybe Sammy had the right idea going after the classy girls.

Dean smirks and glances around at the other men in the bar; they’ve started to dissipate after realizing that the g-man had her attention. “Well, you aren’t wearin’ a wedding ring, so you’re not hitched and in the two minutes I’ve been here, I’ve seen you wave on about five others who’ve been desperately trying to make a pass at the doll in the pretty red dress.”

She blushes and glances down at her glass. “You got me, g-man, I am here alone. I’ve recently lost 180 pounds. I’m here to celebrate.”

He cocks his eyebrow, a little confused.

“Just dumped the cheatin’ bastard,” she laughs.

Dean extends his hand and introduces himself, learns her name is Y/N. Apparently, she’d only been going steady with the guy for a few months. “He seemed a decent guy, you know. A real dreamboat, but then I caught him in bed with another woman so I got rid of his ass. What about you, Casanova? What brings you here?”

Loaded question.

“A little time off before I meet up with partner to finish this case we’re working on,” he says. Technically true, but way off the mark. As per usual in his life. “Can I buy ya another drink?”

“With a face like that, why not,” she replies with a smile. It’s the kind of smile that can ruin a man like Dean.

But what a way to go. “Well, excuse me for a bein’ a little doll dizzy, but would you wanna take this somewhere else?”

“You take me for a charity girl?”

He assumes that means an easy woman, so he chooses his words wisely. “Definitely not. But maybe one who’s looking for a good time.”

“And you think you can show me that?”

Dean bites his lip and slips his hand over hers. “Absolutely.”

Placing money on the counter to cover both their tabs, he escorts her out of the bar and into the cool night air. “My motel is just done the block. Kinda here from outta town.”

“Well, as long as you can show me a good time anywhere, I’m good to go, dreamboat.”

He could get used to her calling him that. But he shakes that thought away and picks up the pace. Though there aren’t many people on the street, those that walk by seem impressed with the woman on his arm. As they approach the motel room, she leans into him, her eyes swirling with mischief. “How do you feel about a lady takin’ charge?” She asks, her cherry red lips forming a smirk that makes him feel things he definitely shouldn’t be feeling. “Lemme show you a good time.”

The key fumbles in the lock, but he manages and when they cross the threshold, she pins him to the wall, peeling the pinstripe suit jacket away from his shoulders. “Oh, the gun holster does things for me Dean.”

“Take a picture in that pretty little head of yours, because I need to take it off to do what I want to do. Need free range of motion.”

His hands skim up the backs of her thighs, gathering the material of her dress so that he can grab what he really wants. “I might be taking off this dress, but that doesn’t mean something else can’t be cherry red.”

Dean kisses her hard and starts to unbutton her dress, pushing it down to reveal the era’s lingerie. He had to admit that modern era lingerie had his approval over this, but if anyone could pull this off it was her.

Hungrily, they cover each other in love bites and kitten licks as they remove the remainder of their clothing. “Alright, doll, get on your hands and knees on the bed and I’ll give you what you need.”

She giggles as she crawls onto the bed, wiggling what is quite possibly one of the perfect asses he’s ever seen. When he rakes his fingers up the right side of her ass, she shivers and leans into the bed. “Trust me?” He whispers.

For some reason, she does. “Spank me, Dean.”

A guttural grunt gets caught in his throat, his cock straining against the boxers he’s still wearing. His hand comes down on her ass, the resounding sound of the smack making him even harder. She whimpers and looks back at him. “Harder.”

He does as she asks, a faint imprint of his hand forming on her soft skin before he moves to the other side. “Have to make sure they match.”

She snickers, crawling backwards and standing bare before him. “Sit,” she says quietly. He stares up with rapt attention, watching the curve of her body as she places herself over his knee; he’s pretty sure he’s died and gone to heaven, but he’s been to heaven before and it ain’t this fun.

A peace falls over, his mind going blank once she sinks into him, her body pliable and ready for whatever he touch he intends to give. He runs his pinky over her slit, she’s already wet. “Already?”

She senses the teasing note in his voice. “Absolutely. I can never seem to find a guy who’ll do this with me.”

Dean’s in awe and then he remembers when he is. “Everyone insist on treating you like a proper lady?”

“And I am,” she says. “I just like it rough.” She gasps the last of her thoughts when his hand comes down on her again. “Fuck.” Each successive slap brings warmth to her already heated skin. Her nerves are alight, the contrast of sharp smacks and his soft touches sending her body into overdrive.

With each hit, she moans, squirming against his clothed cock. “Dean, more, please.”

“Count them. Five each.”

“One, two, three, four,” she counts out in quick succession. “Oh fuck.”

He’s entranced by how wet she is, her juices slipping down the side of her leg. He has six more hits to go but all he can think of is being buried inside her. After one more hit on her right side, he switches to the left, giving her two before stopping himself, allowing her to stew in her own anticipation. 

During the in between beats, he watches how her body reacts, goosebumps prickling her soft skin, arousal dripping, muscles shaking. With the final slaps, she slips to the floor, her body pooling at his feet. She reaches up and pulls his boxers down, allowing his cock to spring free, already dripping with pre-cum. 

When her mouth slips over the tip of his cock, he moans, but even her mouth isn’t enough right now. He crawls backward onto the bed, silently inviting her up to join him. 

The bed dips under her weight, her tongue running up the length of his cock before she straddles him, her legs on either side of his hips. “Want this pretty pussy?”

“Doll, you have no idea.” 

She sinks down onto his cock and whines at the stretch. She’s only been with a couple guys, but none have felt like him, velvet soft and insistently hard. The way his mouth drops open makes her smile; she’s never had this kind of power over a man before, and it’s intoxicating. 

Reaching up, Dean grabs her by the back of the neck and brings her body flush against him. “Right here, doll. Move that ass for me.”  
She moans into his neck, crying out when he grabs the flesh of her ass, the sting from his hands blooming anew. 

Dean moans. “Fuck me.”

Her body moves of its own volition, the pain of his grasp spurring her on. It’s frenetic and driven. And she starts to lose control. He steadies her hips above him and commands her not to move. He wants to watch as he pumps in and out of her. “Look.” He needs her to see it too.

As his cock thrusts upward into her, her breasts bounce with the force. He can’t take it. She’s completely blissed out and it’s all him. Keeping her steady with one hand, he moves the other to her pussy, massaging her clit with his thumb. “Oh hell, Dean. I’m gonna-”

She can’t complete her thought. Her head drops back, mouth agape as she cries out and her walls constrict around him and he’s not far behind.  
Pushing her back, he pulls out and pumps himself roughly, her body still shaking when he comes on her stomach. “Doll, you have no idea what you do to a guy.”

She dips her finger into his release and sucks it off, moaning at the taste. “I have some clue, sugar.”


End file.
